NO890754L - EXPLANATORY MIXTURE, AND PROCEDURE FOR PREPARING SUCH A. - Google Patents
EXPLANATORY MIXTURE, AND PROCEDURE FOR PREPARING SUCH A.Info
- Publication number
- NO890754L NO890754L NO89890754A NO890754A NO890754L NO 890754 L NO890754 L NO 890754L NO 89890754 A NO89890754 A NO 89890754A NO 890754 A NO890754 A NO 890754A NO 890754 L NO890754 L NO 890754L
- Authority
- NO
- Norway
- Prior art keywords
- group
- amines
- alkyl
- emulsion
- aliphatic
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 100
- 238000000034 method Methods 0.000 title claims description 15
- 239000000839 emulsion Substances 0.000 claims description 94
- 239000002360 explosive Substances 0.000 claims description 63
- 239000003995 emulsifying agent Substances 0.000 claims description 56
- -1 aliphatic amines Chemical class 0.000 claims description 53
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 41
- 150000001412 amines Chemical class 0.000 claims description 36
- 239000007859 condensation product Substances 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 23
- 239000003921 oil Substances 0.000 claims description 22
- 229960002317 succinimide Drugs 0.000 claims description 22
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 21
- 229940014800 succinic anhydride Drugs 0.000 claims description 21
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 20
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 19
- 150000003141 primary amines Chemical class 0.000 claims description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical class [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 claims description 15
- 239000000446 fuel Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000012071 phase Substances 0.000 claims description 13
- 239000012188 paraffin wax Substances 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 239000012074 organic phase Substances 0.000 claims description 10
- 239000001384 succinic acid Substances 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 7
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 claims description 6
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000000295 fuel oil Substances 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000012266 salt solution Substances 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 150000003927 aminopyridines Chemical class 0.000 claims description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 3
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000003760 tallow Substances 0.000 claims description 3
- 239000007762 w/o emulsion Substances 0.000 claims description 3
- 239000001993 wax Substances 0.000 claims description 3
- GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical compound FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 2
- 244000060011 Cocos nucifera Species 0.000 claims description 2
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 2
- 150000001334 alicyclic compounds Chemical class 0.000 claims description 2
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910001963 alkali metal nitrate Inorganic materials 0.000 claims description 2
- 229910001964 alkaline earth metal nitrate Inorganic materials 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- KHPLPBHMTCTCHA-UHFFFAOYSA-N ammonium chlorate Chemical compound N.OCl(=O)=O KHPLPBHMTCTCHA-UHFFFAOYSA-N 0.000 claims description 2
- 239000010775 animal oil Substances 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 239000002283 diesel fuel Substances 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 239000010685 fatty oil Substances 0.000 claims description 2
- 229940013317 fish oils Drugs 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000004200 microcrystalline wax Substances 0.000 claims description 2
- 235000019808 microcrystalline wax Nutrition 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000005673 monoalkenes Chemical class 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 150000003738 xylenes Chemical class 0.000 claims description 2
- 244000299461 Theobroma cacao Species 0.000 claims 1
- 235000009470 Theobroma cacao Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 150000001408 amides Chemical class 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 238000003860 storage Methods 0.000 description 7
- 235000011044 succinic acid Nutrition 0.000 description 7
- 229920002367 Polyisobutene Polymers 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000003949 imides Chemical class 0.000 description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 238000007670 refining Methods 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 229940067606 lecithin Drugs 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000010344 sodium nitrate Nutrition 0.000 description 3
- 239000004317 sodium nitrate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000001593 sorbitan monooleate Substances 0.000 description 2
- 235000011069 sorbitan monooleate Nutrition 0.000 description 2
- 229940035049 sorbitan monooleate Drugs 0.000 description 2
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 description 1
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229920000926 Galactomannan Polymers 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 239000000006 Nitroglycerin Substances 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 1
- 239000000026 Pentaerythritol tetranitrate Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- 241000589636 Xanthomonas campestris Species 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005474 detonation Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229920013818 hydroxypropyl guar gum Polymers 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229960004321 pentaerithrityl tetranitrate Drugs 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 244000000003 plant pathogen Species 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- IIQJBVZYLIIMND-UHFFFAOYSA-J potassium;antimony(3+);2,3-dihydroxybutanedioate Chemical compound [K+].[Sb+3].[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O IIQJBVZYLIIMND-UHFFFAOYSA-J 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000015 trinitrotoluene Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B47/00—Compositions in which the components are separately stored until the moment of burning or explosion, e.g. "Sprengel"-type explosives; Suspensions of solid component in a normally non-explosive liquid phase, including a thickened aqueous phase
- C06B47/14—Compositions in which the components are separately stored until the moment of burning or explosion, e.g. "Sprengel"-type explosives; Suspensions of solid component in a normally non-explosive liquid phase, including a thickened aqueous phase comprising a solid component and an aqueous phase
- C06B47/145—Water in oil emulsion type explosives in which a carbonaceous fuel forms the continuous phase
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/22—Amides or hydrazides
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- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Colloid Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Description
Foreliggende oppfinnelse gjelder en emulsjonssprengstoffblanding. The present invention relates to an emulsion explosive mixture.
Kommersielt tilgjengelige emulsjonssprengstoffer er vanligvis av vann-i-olje-typen hvor små dråper av en vandig løsning av en oksygen-avgivende kilde er emulgert i en kontinuerlig, organisk brennstoffase. Slike vann-i-olje-emulsjonssprengstoffblandinger er for eksempel beskrevet i US patenter - 3 447 978, 3 674 578, 3 770 552, 4 104 092, 4 111 727, 4 149 916 og 4 149 917. Commercially available emulsion explosives are usually of the water-in-oil type where small droplets of an aqueous solution of an oxygen-releasing source are emulsified in a continuous, organic fuel phase. Such water-in-oil emulsion explosive mixtures are for example described in US patents - 3,447,978, 3,674,578, 3,770,552, 4,104,092, 4,111,727, 4,149,916 and 4,149,917.
I noen tilfeller kan vanninnholdet i den oksyderende fasen reduseres til meget lave nivåer, for eksempel mindre enn 4%, eller til og med fullstendig elimineres. Slike smelte-i-olje-emulsjonssprengstoffer er for eksempel beskrevet i US patent 4 248 644. I foreliggende beskrivelse omfatter uttrykket "emulsjonssprengstoffblanding" både vann-i-olje- eller smelte-i-olj e-typene. In some cases, the water content of the oxidizing phase can be reduced to very low levels, for example less than 4%, or even completely eliminated. Such melt-in-oil emulsion explosives are, for example, described in US patent 4,248,644. In the present description, the term "emulsion explosive mixture" includes both the water-in-oil or melt-in-oil types.
I disse emulsjonssprengstoffblandingene anvendes overflate-spennings-modifiserende emulgatorer for å fremme oppdeling i den kontinuerlige fasen. Emulgatorene har også en stabiliserende virkning på emulsjonen, og hindrer nedbrytning ved inhibering av sammensmeltning og agglomerering av dråpene. In these emulsion explosive mixtures, surface-tension-modifying emulsifiers are used to promote separation in the continuous phase. The emulsifiers also have a stabilizing effect on the emulsion, and prevent breakdown by inhibiting coalescence and agglomeration of the droplets.
I tillegg er dråpene i den oksyderende fasen i seg selv metastabile og oppviser en tendens til å krystallisere. Krystallvekst ødelegger følsomheten for detonasjon av emulsjons-sprengstof fblandingene og i alvorlige tilfeller kan sammenlåsing av krystaller danne en fast blanding som er meget vanskelig å tenne. Slike emulsjonssprengstoffblandinger har en tilbøyelighet til progressiv nedbrytning av sprengstoffytelse under lagring og transport av sprengstoffene før bruk. Videre har forskjellige additiver som for eksempel fast ammoniumnitrat og mikroballonger, som vanligvis anvendes i emulsjonssprengstoffer, en tendens til å virke som kjernedannende midler og kan føre til, eller øke, krystallveksten. In addition, the droplets in the oxidizing phase are themselves metastable and exhibit a tendency to crystallize. Crystal growth destroys the sensitivity to detonation of the emulsion-explosive mixtures and in severe cases interlocking of crystals can form a solid mixture which is very difficult to ignite. Such emulsion explosive mixtures have a propensity for progressive degradation of explosive performance during storage and transport of the explosives prior to use. Furthermore, various additives such as solid ammonium nitrate and microballoons, which are usually used in emulsion explosives, tend to act as nucleating agents and can lead to, or increase, crystal growth.
Forskjellige emulgatortyper og -blandinger er beskrevet på fagområdet. Australsk patentsøknad nr. 40006/85 (Cooper og Baker) beskriver emulsjonssprengstoffblandinger i hvilke emulgatoren er et ledningsevne modifiseringsmiddel. Inkludert blant alike emulgatorer er kondensasjonsprodukter av poly- Different emulsifier types and mixtures are described in the subject area. Australian Patent Application No. 40006/85 (Cooper and Baker) discloses emulsion explosive compositions in which the emulsifier is a conductivity modifier. Included among similar emulsifiers are condensation products of poly-
[alk(en)yl]ravsyre-anhydrid med primære aminer som for eksempel etylendiamin, dietyltriamin, dimetylaminopropylamin og etanolamin. [alk(en)yl]succinic anhydride with primary amines such as ethylenediamine, diethyltriamine, dimethylaminopropylamine and ethanolamine.
Kondensasjonsreaksjonen mellom et primært amin og poly-[alk(en)yl]ravsyre eller -anhydrid kan produsere et amid-og/eller et imid kondensasjonsprodukt. For eksempel kan reaksjon mellom etanolamin og poly[alk(en)yl] ravsyreanhydrid gi hvilke som helst av produktene med formel Ia, Ib og II hvor A er poly[alk(en)yl]. The condensation reaction between a primary amine and poly-[alk(en)yl]succinic acid or -anhydride can produce an amide and/or an imide condensation product. For example, reaction between ethanolamine and poly[alk(en)yl] succinic anhydride can give any of the products of formula Ia, Ib and II where A is poly[alk(en)yl].
Typisk dannes det under standard reaksjonsbetingelser en blanding av amid- og imidkondensasjonsprodukter. Amider dannes raskere og under mindre krevende betingelser enn imider, og således er hovedmengden av kondensasjonsproduktet amid. Det er faktisk funnet at et høyt amidinnhold er ønskelig. Typically, a mixture of amide and imide condensation products is formed under standard reaction conditions. Amides are formed faster and under less demanding conditions than imides, and thus the main amount of the condensation product is amide. Indeed, it has been found that a high amide content is desirable.
Søkerne har fått bekreftelse på den utmerkede lagrings-stabiliteten til emulsjonsblandinger omfattende slike modi-fiseringsmidler og har overraskende funnet at stabiliteten av spesielle emulsjonsblandinger økes dersom emulgeringsmidlet omfatter et kondensasjonsprodukt av et primært amin og en poly-[alk(en)yl]ravsyre eller -anhydrid som omfatter en høy andel av suksinimidproduktet med formel II. The applicants have received confirmation of the excellent storage stability of emulsion mixtures comprising such modifiers and have surprisingly found that the stability of particular emulsion mixtures is increased if the emulsifier comprises a condensation product of a primary amine and a poly-[alk(en)yl]succinic acid or - anhydride comprising a high proportion of the succinimide product of formula II.
Ifølge oppfinnelsen tilveiebringes derfor en emulsjons-sprengstof fblanding omfattende en diskontinuerlig fase omfattende et oksygen-avgivende salt, en kontinuerlig, vann-ublandbar, organisk fase og et emulgeringsmiddel omfattende et kondensasjonsprodukt av et primært amin og en poly[alk(en)yl]ravsyre eller -anhydrid og hvori kondensasjonsproduktet omfatter minst 70 vekt% av suksinimidproduktet. According to the invention, there is therefore provided an emulsion-explosive mixture comprising a discontinuous phase comprising an oxygen-releasing salt, a continuous, water-immiscible, organic phase and an emulsifier comprising a condensation product of a primary amine and a poly[alk(en)yl]succinic acid or -anhydride and in which the condensation product comprises at least 70% by weight of the succinimide product.
Uttrykket "primært amin" refererer til forbindelser omfattende minst en primæraminandel. The term "primary amine" refers to compounds comprising at least one primary amine moiety.
I poly[alk(en)yl]ravsyren og/eller -anhydridet omfatter fortrinnsvis poly[alk(en)yl]-andelen en ryggradsekvens i området på fra 10 til 500 sammenbundne atomer som kan være karbonatomer, eller i hovedsak karbonatomer avbrudt av hetero-atomer som for eksempel oksygen eller nitrogen. In the poly[alk(en)yl]succinic acid and/or -anhydride, the poly[alk(en)yl] part preferably comprises a backbone sequence in the range of from 10 to 500 connected atoms which may be carbon atoms, or essentially carbon atoms interrupted by hetero -atoms such as oxygen or nitrogen.
En spesielt foretrukken poly[alk(en)yl] er en mettet eller umettet hydrokarbonkjede som er en polymer av et mono-olefin, idet polymerkjeden inneholder i området på fra 40 til 500 karbonatomer. Eksempler på slike polyolefiner omfatter de som er oppnådd fra C2-Cg-olefin som for eksempel etylen, propylen, 1-buten, isopren og isobuten. A particularly preferred poly[alk(en)yl] is a saturated or unsaturated hydrocarbon chain which is a polymer of a mono-olefin, the polymer chain containing in the range of from 40 to 500 carbon atoms. Examples of such polyolefins include those obtained from C2-C8 olefins such as ethylene, propylene, 1-butene, isoprene and isobutene.
Spesielt foretrukken poly[alk(en)yl] er poly(isobutylen)Particularly preferred poly[alk(en)yl] is poly(isobutylene)
og fortrinnsvis er molekylvekten til poly[alk(en)yl]-delen i området på fra 200 til 5000 og mere foretrukket 400 til 2000. and preferably the molecular weight of the poly[alk(en)yl] part is in the range of from 200 to 5000 and more preferably 400 to 2000.
Eksempler på primære aminer omfatter alifatiske aminer, cykloalifatiske aminer, aromatiske aminer og heteroaromatiske aminer, hvilke primære aminer eventuelt kan være substituert med en eller flere substituenter. Examples of primary amines include aliphatic amines, cycloaliphatic amines, aromatic amines and heteroaromatic amines, which primary amines may optionally be substituted with one or more substituents.
Alifatiske aminer kan omfatte alifatiske C-L-C20 aminer hvor den alifatiske kjeden kan være lineær eller forgrenet. Fortrinnsvis er det alifatiske aminet et C^-C2o_alkylamim. Spesielle eksempler på alifatiske aminer omfatter etylamin, n-butylamin, allylamin, kokos-amin, talgamin og laurylamin. Aliphatic amines may include aliphatic C-L-C 20 amines where the aliphatic chain may be linear or branched. Preferably, the aliphatic amine is a C 1 -C 20 alkyl amine. Specific examples of aliphatic amines include ethylamine, n-butylamine, allylamine, coconut amine, tallow amine and laurylamine.
Eksempler på foretrukne substituerte, alifatiske aminer omfatter: hydroksy(Cj-C^Q-alkyl)aminer som for eksempel etanolamin og 3-hydroksypropylamin, amino (C^-C^Q-alkyl)amin som for eksempel aminoetylamin, (Ci-C-LQ-alkyl) aminer substituert med gruppen amino(C1-C1o~alkyl)amino- som for eksempel dietylentriamin (Ci-C^ø-alkyl)amin substituert med gruppen N,N-di(Ci~Examples of preferred substituted aliphatic amines include: hydroxy(Ci-C^Q-alkyl)amines such as ethanolamine and 3-hydroxypropylamine, amino (Ci-C^Q-alkyl)amine such as aminoethylamine, (Ci-C -LQ-alkyl) amines substituted with the group amino(C1-C10~alkyl)amino- such as for example diethylenetriamine (Ci-C^ø-alkyl)amine substituted with the group N,N-di(Ci~
C4alkyl)amino (som for eksempel dimetylaminopropylamin, fenyl (C^-C^o-alkyl) aminer som for eksempel benzylamin og heterocykliske, substituerte (C^-C^Q-alkyl)aminer slik som beskrevet i australsk patentsøknad nr. PI 6920. C 4 alkyl)amino (such as dimethylaminopropylamine, phenyl (C 1 -C 20 alkyl) amines such as benzylamine and heterocyclic substituted (C 1 -C 4 alkyl)amines as described in Australian Patent Application No. PI 6920 .
Eksempler på cykloalifatiske aminer omfatter cykloheksylamin og cyclopentylamin. Aromatiske aminer omfatter anilin. Heteroaromatiske aminer omfatter aminopyridiner. Examples of cycloaliphatic amines include cyclohexylamine and cyclopentylamine. Aromatic amines include aniline. Heteroaromatic amines include aminopyridines.
Foretrukne primære aminer omfatter (C1-C4-alkyl)aminer, spesielt etanolamin, og N-N, di(C1-C4-alkyl)amino( C^ C^-alkyl)aminer, spesielt dimetylaminopropylamin. Preferred primary amines include (C 1 -C 4 alkyl)amines, especially ethanolamine, and N-N,di(C 1 -C 4 alkyl)amino(C 1 -C 4 alkyl)amines, especially dimethylaminopropylamine.
I emulsjonssprengstoffblandinger ifølge foreliggende oppfinnelse er det et essensielt trekk at minst 70 vekt% av kondensasjonsproduktet i emulgatorkomponenten er suksinimidforbindelsen. Slike blandinger raffineres overraskende generelt lettere enn tilsvarende blandinger omfattende en signifikant del amidkondensasjonsprodukter. Dette gjør det mulig å fremstille og raffinere blandingene ifølge foreliggende oppfinnelse til en gitt dråpestørrelse raskere og med bruk av mindre energi. Fortrinnsvis vil minst 85 vekt% av konden-sasj onsproduktet være suksinimidproduktet. Mere foretrukket vil minst 90 vekt% av kondensasjonsproduktet være suksinimidproduktet. Mest foretrukket er i det vesentlige hele konden-sasj onsproduktet suksinimidproduktet. In emulsion explosive mixtures according to the present invention, it is an essential feature that at least 70% by weight of the condensation product in the emulsifier component is the succinimide compound. Such mixtures are surprisingly generally refined more easily than corresponding mixtures comprising a significant proportion of amide condensation products. This makes it possible to prepare and refine the mixtures according to the present invention to a given droplet size faster and with the use of less energy. Preferably, at least 85% by weight of the condensation product will be the succinimide product. More preferably, at least 90% by weight of the condensation product will be the succinimide product. Most preferably, essentially the entire condensation product is the succinimide product.
Egnede oksygen-avgivende salter for bruk i blandingen ifølge oppfinnelsen omfatter alkali- og jordalkalimetall-nitratene, -kloratene og -perkloratene, ammoniumnitrat, ammoniumklorater, ammoniumperklorat og blandinger derav. De foretrukne, oksygen-avgivende saltene omfatter ammoniumnitrat, natriumnitrat og kalsiumnitrat. Mere foretrukket omfatter det oksygen-avgivende saltet ammoniumnitrat eller en blanding av ammoniumnitrat og natrium- eller kalsiumnitrater. Suitable oxygen-releasing salts for use in the composition according to the invention include the alkali and alkaline earth metal nitrates, chlorates and perchlorates, ammonium nitrate, ammonium chlorates, ammonium perchlorate and mixtures thereof. The preferred oxygen-releasing salts include ammonium nitrate, sodium nitrate and calcium nitrate. More preferably, the oxygen-releasing salt comprises ammonium nitrate or a mixture of ammonium nitrate and sodium or calcium nitrates.
Typisk omfatter den oksygen-avgivende saltbestanddelen i blandingene ifølge foreliggende oppfinnelse fra 45 til 95 og fortrinnsvis fra 60 til 90 vekt% av totalblandingen. Typically, the oxygen-releasing salt component in the mixtures according to the present invention comprises from 45 to 95 and preferably from 60 to 90% by weight of the total mixture.
I blandinger der det oksygen-avgivende saltet omfatter en blanding av ammoniumnitrat og natriumnitrat er det foretrukne sammensetningsområdet for en slik blanding fra 5 til 80 deler natriumnitrat for hver 100 deler ammoniumnitrat. Spesielt omfatter de foretrukne blandingene ifølge foreliggende oppfinnelse en oksygen-avgivende saltbestanddel bestående av 60 til 90 vekt% (av totalblandingen) ammoniumnitrat eller blandinger av fra 0 til 40 vekt% (av totalblandingen) natrium- eller kalsiumnitrater og fra 50 til 90 vekt% (av totalblandingen) ammoniumnitrat. In mixtures where the oxygen-releasing salt comprises a mixture of ammonium nitrate and sodium nitrate, the preferred composition range for such a mixture is from 5 to 80 parts sodium nitrate for every 100 parts ammonium nitrate. In particular, the preferred mixtures according to the present invention comprise an oxygen-releasing salt component consisting of 60 to 90% by weight (of the total mixture) ammonium nitrate or mixtures of from 0 to 40% by weight (of the total mixture) sodium or calcium nitrates and from 50 to 90% by weight ( of the total mixture) ammonium nitrate.
Typisk er den mengde vann som anvendes i blandingeneTypical is the amount of water used in the mixtures
ifølge foreliggende oppfinnelse i området på fra 0 til 30 vekt% av totalblandingen. Fortrinnsvis er den anvendte mengde fra 4 til 25, og mere foretrukket fra 6 til 20, vekt% av totalblandingen. according to the present invention in the range of from 0 to 30% by weight of the total mixture. Preferably, the amount used is from 4 to 25, and more preferably from 6 to 20, weight% of the total mixture.
Den vann-ublandbare, organiske fasen i blandingen ifølge foreliggende oppfinnelse omfatter den kontinuerlige "olje"-fasen i emulsjonssprengstoffet og er brennstoffet. Egnede organiske brennstoffer for bruk i den vann-ublandbare, organiske fasen omfatter alifatiske, alicykliske og aromatiske forbindelser og blandinger derav som er i flytende tilstand ved sammenblandingstemperaturen. Egnede organiske brennstoffer kan velges fra brenselolje, dieselolje, destillat, fyringsolje, petroleum, nafta, voks, (for eksempel mikrokrystallinsk voks, parafinvoks og råparafin), parafinoljer, benzen, toluen, exylener, asfalt-materialer, polymere oljer som for eksempel polymerer med lav molekylvekt av olefiner, animalske oljer, fiskeoljer, og andre mineralske, hydrokarbon- eller fettoljer, og blandinger derav. Foretrukne organiske brennstoffer er flytende hydrokarboner, generelt referert til som petroleumdestillater, som for eksempel bensin, petroleum, brenseloljer og parafinoljer. The water-immiscible, organic phase in the mixture according to the present invention comprises the continuous "oil" phase in the emulsion explosive and is the fuel. Suitable organic fuels for use in the water-immiscible organic phase include aliphatic, alicyclic and aromatic compounds and mixtures thereof which are in a liquid state at the mixing temperature. Suitable organic fuels can be selected from fuel oil, diesel oil, distillate, heating oil, petroleum, naphtha, wax, (for example microcrystalline wax, paraffin wax and crude paraffin), paraffin oils, benzene, toluene, xylenes, asphalt materials, polymeric oils such as polymers with low molecular weight olefins, animal oils, fish oils, and other mineral, hydrocarbon or fatty oils, and mixtures thereof. Preferred organic fuels are liquid hydrocarbons, generally referred to as petroleum distillates, such as gasoline, petroleum, fuel oils and paraffin oils.
Typisk omfatter det organiske brennstoffet eller den kontinuerlige fasen i emulsjonssprengstoffblandingen ifølge oppfinnelsen fra 2 til 15 vekt% og fortrinnsvis 3 til 10 vekt% av totalblandingen. Typically, the organic fuel or the continuous phase in the emulsion explosive mixture according to the invention comprises from 2 to 15% by weight and preferably 3 to 10% by weight of the total mixture.
Emulgatorbestanddelen i blandingen ifølge foreliggende oppfinnelse kan videre omfatte tilleggsemulgatorer valgt fra det brede område av emulgatorer som på fagområdet er kjent å være anvendbare ved fremstilling av emulsjonssprengstoffblandinger. Eksempler på slike emulgatorer omfatter alkohol-alkoksylater, fenolalkoksylater, poly(oksyalkylen)glykoler, poly(oksyalkylen)fettsyreestere, aminalkoksylater, fettsyreestere av sorbitol og glycerol, fettsyresalter, sorbitanestere, poly(oksyalkylen)sorbitanestere, fettaminalkoksylater, poly- The emulsifier component in the mixture according to the present invention can further comprise additional emulsifiers selected from the wide range of emulsifiers which are known in the field to be applicable in the production of emulsion explosive mixtures. Examples of such emulsifiers include alcohol alkoxylates, phenol alkoxylates, poly(oxyalkylene)glycols, poly(oxyalkylene)fatty acid esters, aminalkoxylates, fatty acid esters of sorbitol and glycerol, fatty acid salts, sorbitan esters, poly(oxyalkylene)sorbitan esters, fatty amino alkylates, poly-
(oksyalkylen)glykolestere, fettsyreamidalkoksylater, fett-aminer, quaternære aminer, alkyloxazoliner, alkenyloxazoliner, imidazoliner, alkyl-sulfonater, alkylarylsulfonater, alkylsulfo-suksinater, alkylfosfater, alkenylfosfater, fosfatestere, lecitin, kopolymerer av poly(oxyalkylen)glykoler og poly(12-hydroksystearinsyre), og blandinger derav. Blant de foretrukne emulgatorene er 2-alkyl- og 2-alkenyl-4,4 *-bis (hydroksymetyl) oxazolin, fettsyreesterne av sorbitol, lecitin, kopolymerer av poly(oxyalkylen)glykoler og poly(12-hydroksystearinsyre) og blandinger derav, og spesielt sorbitanmonooleat, sorbitan-sesquioleat, 2-oleyl- 4,4'-bis (hydroksymetyl)oxazolin, blandinger av sorbitan sesquioleat, lecitin og en kopolymer av poly(oxyalkylen)glykol og poly(12-hydroksystearinsyre), og blandinger derav. Når de anvendes omfatter spesielt foretrukne, ytterligere emulgatorer sorbitanestere som for eksempel sorbitan-monooleat. (oxyalkylene)glycol esters, fatty acid amidal oxylates, fatty amines, quaternary amines, alkyloxazolines, alkenyloxazolines, imidazolines, alkylsulfonates, alkylarylsulfonates, alkylsulfosuccinates, alkylphosphates, alkenylphosphates, phosphate esters, lecithin, copolymers of poly(oxyalkylene)glycols and poly(12- hydroxystearic acid), and mixtures thereof. Among the preferred emulsifiers are 2-alkyl- and 2-alkenyl-4,4*-bis(hydroxymethyl)oxazoline, the fatty acid esters of sorbitol, lecithin, copolymers of poly(oxyalkylene)glycols and poly(12-hydroxystearic acid) and mixtures thereof, and in particular sorbitan monooleate, sorbitan sesquioleate, 2-oleyl-4,4'-bis(hydroxymethyl)oxazoline, mixtures of sorbitan sesquioleate, lecithin and a copolymer of poly(oxyalkylene)glycol and poly(12-hydroxystearic acid), and mixtures thereof. When used, particularly preferred additional emulsifiers include sorbitan esters such as sorbitan monooleate.
Typisk omfatter emulgatorbestanddelen i blandingen ifølge foreliggende oppfinnelse opptil 5 vekt% av totalblandingen. Større mengder emulgeringsmiddel kan anvendes og kan tjene som et tilleggsbrennstoff for blandingen, men generelt er det ikke nødvendig å tilsette mer enn 5 vekt% emulgeringsmiddel for å oppnå ønsket effekt. En av fordelene med blandingene ifølge foreliggende oppfinnelse er at det kan fremstilles stabile emulsjoner ved bruk av relativt små mengder emulgator, og av økonomiske grunner foretrekkes det å holde mengden emulgator på det minimum som kreves for å oppnå ønsket effekt. Den foretrukne mengde emulgator som anvendes, er i området fra 0,1 til 2,0 vekt% av totalblandingen. Typically, the emulsifier component in the mixture according to the present invention comprises up to 5% by weight of the total mixture. Larger amounts of emulsifier can be used and can serve as an additional fuel for the mixture, but generally it is not necessary to add more than 5% by weight of emulsifier to achieve the desired effect. One of the advantages of the mixtures according to the present invention is that stable emulsions can be produced using relatively small amounts of emulsifier, and for economic reasons it is preferred to keep the amount of emulsifier to the minimum required to achieve the desired effect. The preferred amount of emulsifier used is in the range from 0.1 to 2.0% by weight of the total mixture.
Om ønsket kan andre eventuelle brennstoffer, heretter referert til som sekundære brennstoffer, innblandes i blandingene ifølge foreliggende oppfinnelse i tillegg til den vann-ublandbare, organiske brennstoffasen. Eksempler på slike sekundære brennstoffer omfatter findelte faststoffer, og vann-ublandbare, organiske væsker som kan anvendes for delvis å erstatte vann som løsningsmiddel for de oksygen-avgivende saltene eller for å fortynne det vandige løsningsmidlet for de oksygen-avgivende saltene. Eksempler på faste, sekundære brennstoffer omfatter findelte materialer som for eksempel: svovel, aluminiun og karbonholdige materialer som for eksempel gilsonitt, findelt koks eller kull, kjønnrøk, harpikssyre som for eksempel abietinsyre, sukre som for eksempel glukose eller dextrose og andre vegetabilske produkter som for eksempel stivelse, nøttemel, kornmel og tremasse. Eksempler på vann-blandbare, organiske væsker omfatter alkoholer som for eksempel metanol, glykoler som for eksempel etylenglykol, amider som for eksempel formamid og aminer som for eksempel metylamin. If desired, other possible fuels, hereinafter referred to as secondary fuels, can be mixed into the mixtures according to the present invention in addition to the water-immiscible, organic fuel phase. Examples of such secondary fuels include finely divided solids, and water-immiscible organic liquids that can be used to partially replace water as solvent for the oxygen-releasing salts or to dilute the aqueous solvent for the oxygen-releasing salts. Examples of solid, secondary fuels include finely divided materials such as: sulphur, aluminum and carbonaceous materials such as gilsonite, finely divided coke or coal, black smoke, resin acids such as abietic acid, sugars such as glucose or dextrose and other vegetable products such as for example starch, nut flour, grain flour and wood pulp. Examples of water-miscible organic liquids include alcohols such as methanol, glycols such as ethylene glycol, amides such as formamide and amines such as methylamine.
Typisk omfatter det eventuelle, sekundære brennstoffet i blandingen ifølge foreliggende oppfinnelse fra 0 til 3 0 vekt% av totalblandingen. Typically, the possible secondary fuel in the mixture according to the present invention comprises from 0 to 30% by weight of the total mixture.
Det ligger innenfor oppfinnelsen at det også kan innblandes andre substanser eller blandinger av substanser som er oksygen-avgivende salter eller som i seg selv er egnet som sprengstoffmaterialer i de foran beskrevne emulsjonssprengstoffblandingene. Som et typisk eksempel på en slik modifisert emulsjonsspreng-stof fblanding refereres det til blandinger hvori det tilsettes til og blandes med en emulsjonssprengstoffblanding som beskrevet foran opp til 9 0% vekt/vekt av et oksyderende salt som for eksempel ammoniumnitrat og brenselolje og som vanligvis refereres til av fagmannen som "anfo". Sammensetningene av "anfo" er vel kjent og er ofte beskrevet i litteratur som gjelder sprengstoffer. Det ligger også innenfor oppfinnelsen å tilsette som en ytterligere sprengstoffbestandel til blandingen velkjente sprengstoffmaterialer omfattende en eller flere av for eksempel trinitrotoluen, nitroglycerin eller pentaerytritol tetranitrat. It is within the scope of the invention that other substances or mixtures of substances which are oxygen-releasing salts or which in themselves are suitable as explosive materials can also be mixed into the emulsion explosive mixtures described above. As a typical example of such a modified emulsion explosive mixture, reference is made to mixtures in which it is added to and mixed with an emulsion explosive mixture as described above up to 90% weight/weight of an oxidizing salt such as ammonium nitrate and fuel oil and which is usually referred to to the professional as "anfo". The compositions of "anfo" are well known and are often described in literature relating to explosives. It is also within the scope of the invention to add as a further explosive component to the mixture well-known explosive materials comprising one or more of, for example, trinitrotoluene, nitroglycerin or pentaerythritol tetranitrate.
Det tilveiebringes således en sprengstoffblanding omfattende som en første bestanddel en emulsjonssprengstoffblanding som beskrevet foran og som en andre bestanddel en mengde av et materiale som er et oksyderende salt eller som i seg selv er et sprengstoffmateriale. An explosive mixture is thus provided comprising as a first component an emulsion explosive mixture as described above and as a second component an amount of a material which is an oxidizing salt or which is itself an explosive material.
Om ønsket kan den vandige løsningen av blandingene ifølge foreliggende oppfinnelse omfatte eventuelle fortykningsmidler som eventuelt kan være tverrbundet. Når det anvendes fortykningsmidler i blandingene ifølge foreliggende oppfinnelse, er de passende polymere materialer, spesielt gummimaterialer av typen galaktomannangummier som for eksempel johannes brød gummi eller guargummi eller derivater derav som for eksempel hydroksy-propylguargummi. Andre anvendbare, men mindre foretrukne, gummier er de såkalte biopolymere gummiene som for eksempel de heteropolysakkarider som fremstilles ved mikrobiell omdannelse av karbohydratmateriale, for eksempel behandlingen av glukose med et plantepatogen av slekten Xanthomonas, typisk Xanthomonas campestris. Andre anvendbare fortykningsmidler omfatter syntetiske, polymere materialer og spesielt syntetiske, polymere materialer som i det minste delvis er oppnådd fra monomeren akrylamid. If desired, the aqueous solution of the mixtures according to the present invention may include any thickeners which may possibly be cross-linked. When thickeners are used in the mixtures according to the present invention, they are suitable polymeric materials, especially rubber materials of the type galactomannan gums such as locust bean gum or guar gum or derivatives thereof such as hydroxypropyl guar gum. Other applicable, but less preferred, gums are the so-called biopolymeric gums such as the heteropolysaccharides produced by microbial conversion of carbohydrate material, for example the treatment of glucose with a plant pathogen of the genus Xanthomonas, typically Xanthomonas campestris. Other useful thickeners include synthetic polymeric materials and in particular synthetic polymeric materials derived at least in part from the monomer acrylamide.
Typisk omfatter det eventuelle fortykningsmidlet i foreliggende oppfinnelse fra 0 til 2 vekt% av totalblandingen. Typically, the optional thickener in the present invention comprises from 0 to 2% by weight of the total mixture.
Når fortykningsmidler anvendes i blandingene ifølge foreliggende oppfinnelse kan det som angitt ovenfor være tverrbundet. Det er for dette formål hensiktsmessig å anvende konvensjonelle tverrbindingsmidler som for eksempel sinkkromat eller et dikromat enten som en separat enhet eller som en bestanddel av et konvensjonelt redox-system som for eksempel en blanding av kaliumdikromat og kaliumantimontartrat. When thickeners are used in the mixtures according to the present invention, they may be cross-linked as stated above. For this purpose, it is appropriate to use conventional cross-linking agents such as zinc chromate or a dichromate either as a separate unit or as a component of a conventional redox system such as a mixture of potassium dichromate and potassium antimony tartrate.
Typisk omfatter det eventuelle tverrbindingsmidlet i blandingene ifølge foreliggende oppfinnelse fra 0 til 0,5 og fortrinnsvis fra 0 til 0,1 vekt% av totalblandingen. Typically, the possible cross-linking agent in the mixtures according to the present invention comprises from 0 to 0.5 and preferably from 0 to 0.1% by weight of the total mixture.
PH i emulsjonsprengstoffblandingene ifølge foreliggende oppfinnelse er ikke strengt kritisk. Generelt er imidlertid pH mellom 0 og 8 og fortrinnsvis er pH mellom 1 og 6, og kan reguleres ved passende tilsetning av konvensjonelle additiver, for eksempel uorganiske eller organiske syrer og salter. The pH in the emulsion explosive mixtures according to the present invention is not strictly critical. In general, however, the pH is between 0 and 8 and preferably the pH is between 1 and 6, and can be regulated by suitable addition of conventional additives, for example inorganic or organic acids and salts.
I en utførelsesform av foreliggende oppfinnelse tilveiebringes en emulgatorkomponent omfattende et kondensasjonsprodukt av et primært amin og en poly[alk(en)yl]ravsyre eller -anhydrid og hvori kondensasjonsproduktet omfatter minst 7 0 vekt% av suksinimidproduktet. In one embodiment of the present invention, an emulsifier component comprising a condensation product of a primary amine and a poly[alk(en)yl]succinic acid or anhydride is provided and in which the condensation product comprises at least 70% by weight of the succinimide product.
Foretrukne, primære aminer og poly[alk(en)yl]ravsyrer og/eller -anhydrider er som definert ovenfor. Foretrukne mengder av suksinimidprodukt er som definert foran. Preferred primary amines and poly[alk(en)yl]succinic acids and/or anhydrides are as defined above. Preferred amounts of succinimide product are as defined above.
Emulgatorbestanddelen kan fremstilles ved hjelp av forskjellige fremgangsmåter for omsetning av det primære aminet med ravsyren eller anhydridbestanddelen og reaksjonsbetingelsene kan velges for å tilveiebringe den høye andelen av suksinimin-forbindelse som karakteriserer blandingene ifølge oppfinnelsen. The emulsifier component can be prepared by various methods for reacting the primary amine with the succinic acid or the anhydride component and the reaction conditions can be chosen to provide the high proportion of succinimine compound which characterizes the compositions according to the invention.
Aminet og poly[alk(en)yl]ravsyreanhydridet kan oppvarmes i et målforhold på 1:1, eventuelt i nærvær av et løsningsmiddel eller fortynningsmiddel som for eksempel et organisk brennstoff. Generelt er det hensiktsmessig å utføre reaksjonen ved relativt høye temperaturer for effektivt å fremstille en høy andel suksinimid. For eksempel kan det fremstilles et kondensasjonsprodukt av et etanolamin og polyisobutylen ravsyreanhydrid omfattende godt over 95 vekt% suksinimidprodukt ved å oppvarme reaktantene i et målforhold på ca. 1:1 ved en temperatur på ca. 140 til 160°C i 2 timer. Lavere temperaturer kan anvendes med tilsvarende økning i reaksjonstider eller ved aktivt å fjerne vann fra reaksjonen under vakuum eller ved bruk av et Dean og Stark apparat og et passende løsningsmiddel. The amine and the poly[alk(en)yl]succinic anhydride can be heated in a target ratio of 1:1, optionally in the presence of a solvent or diluent such as an organic fuel. In general, it is appropriate to carry out the reaction at relatively high temperatures in order to efficiently produce a high proportion of succinimide. For example, a condensation product of an ethanolamine and polyisobutylene succinic anhydride comprising well over 95% by weight of succinimide product can be prepared by heating the reactants in a target ratio of approx. 1:1 at a temperature of approx. 140 to 160°C for 2 hours. Lower temperatures can be used with a corresponding increase in reaction times or by actively removing water from the reaction under vacuum or by using a Dean and Stark apparatus and a suitable solvent.
Generelt foretrekkes det at reaksjonstemperaturen for fremstilling av produktet med høyt suksinimidinnhold er minst 100°C og fortrinnsvis i området 100 til 160°C. In general, it is preferred that the reaction temperature for producing the product with a high succinimide content is at least 100°C and preferably in the range of 100 to 160°C.
Ved temperaturer under 100°C er det generelt nødvendig å anvende lange reaksjonstider, av størrelsesorden flere dager eller mer for å tilveiebringe et høyt nivå av suksinimid-forbindelse i produktet. At temperatures below 100°C, it is generally necessary to use long reaction times, of the order of several days or more, to provide a high level of succinimide compound in the product.
Emulsjonssprengstoffblandingene ifølge foreliggende oppfinnelse kan fremstilles ved hjelp av en rekke fremgangsmåter. Når blandingen er et emulsjonssprengstoff av vann-i-olje-typen, omfatter en foretrukken fremstillingsmetode: oppløsning av de oksygen-avgivende saltene i vann ved en temperatur over "fudge" punktet for løsningen, fortrinnsvis ved en temperatur i området fra 25 til 110°C, for å gi en vandig saltløsning, kombinering av denne vandige saltløsningen, den vann-ublandbare, organiske fasen og emulgatorbestanddelen, med rask blanding for å danne en vann-i-olje-emulsjon og blanding inntil emulsjonen er jevn. The emulsion explosive mixtures according to the present invention can be produced using a number of methods. When the composition is a water-in-oil type emulsion explosive, a preferred method of preparation comprises: dissolving the oxygen-releasing salts in water at a temperature above the "fudge" point of the solution, preferably at a temperature in the range of 25 to 110° C, to give an aqueous salt solution, combining this aqueous salt solution, the water-immiscible organic phase and the emulsifier component, with rapid mixing to form a water-in-oil emulsion and mixing until the emulsion is smooth.
Oppfinnelsen skal nå forklares, men på ingen måte begrenses, ved hjelp av følgende eksempler i hvilke alle deler og prosenter et på vektbasis om ikke annet er angitt. The invention shall now be explained, but in no way limited, by means of the following examples in which all parts and percentages are by weight unless otherwise stated.
Ved fremstillingen av emulgatorene er det ofte hensiktsmessig å tilveiebringe poly[alk(en)yl]ravsyreanhydridet eller - syren i et oljefortynningsniddel. Slike blandinger er kommer sielt tilgjengelige. For å unngå behovet for å separere kondensasjonsproduktet fra oljefortynningsmidlet kan blandingen tilsettes til den vann-ublandbare, organiske fasen i emulsjons-sprengstof f et og olje-fortynningsmidlet anses som en del av den vann-ublandbare, organiske fasen. Dersom således poly[alk(en)yl] ravsyreanhydridet eller -syren tilveiebringes i et paraffinfortynningsmiddel, kan paraffinfortynningsmidlet anses som en del av den vann-ublandbare, organiske fasen for det formål å definere sammensetningen av emulsjonssprengstoffet. When producing the emulsifiers, it is often appropriate to provide the poly[alk(en)yl]succinic anhydride or acid in an oil dilution vessel. Such mixtures are readily available. To avoid the need to separate the condensation product from the oil diluent, the mixture can be added to the water-immiscible organic phase of the emulsion explosive and the oil diluent considered part of the water-immiscible organic phase. Thus, if the poly[alk(en)yl] succinic anhydride or acid is provided in a paraffin diluent, the paraffin diluent may be considered part of the water-immiscible organic phase for the purpose of defining the composition of the emulsion explosive.
I de følgende eksemplene er det funnet hensiktsmessig å anvende viskositet som en indikator på dråpestørrelsen i emulsjonssprengstoffet som har i det vesentlige samme sammensetning. For å illustrere oppfinnelsen fremstilles for eksempel emulsjonssprengstoffer med samme sammensetning bortsett fra at emulgatorene er av et standard imid/amid-forhold eller et høyt imidforhold. Ved å fremstille disse emulsjonene under faste betingelser utgjør viskositeten en hensiktsmessig indikator på relative dråpestørrelser. In the following examples, it has been found appropriate to use viscosity as an indicator of the droplet size in the emulsion explosive, which has essentially the same composition. To illustrate the invention, for example, emulsion explosives are produced with the same composition except that the emulsifiers are of a standard imide/amide ratio or a high imide ratio. By preparing these emulsions under fixed conditions, the viscosity is a convenient indicator of relative droplet sizes.
Emulsjonene ble fremstilt med en Hobart N50 planetblander. The emulsions were prepared with a Hobart N50 planetary mixer.
Emulatorfremstillinq 1 (EP1)Emulator Making 1 (EP1)
Monoetanolamin ble tilsatt til "MOBILAD"* C207 i et molforhold på 1:1 med hensyn på polyisobutylen ravsyreanhydrid. Monoethanolamine was added to "MOBILAD"* C207 in a molar ratio of 1:1 with respect to polyisobutylene succinic anhydride.
(<*>MOBILAD er et varemerke). MOBILAD C207 er et poly(iso-butylen)ravsyreanhydrid med molekylvekt i området på fra 700 (<*>MOBILAD is a trademark). MOBILAD C207 is a poly(iso-butylene) succinic anhydride with a molecular weight in the range from 700
til 1200 i et paraffinfortynningsmiddel tilgjengelig fra Mobil Oil Co. Ltd. Innholdet av poly(isobutylen)-ravsyreanhydrid i MOBILAD C2 07 er 0,76 mmol/g. to 1200 in a paraffin thinner available from Mobil Oil Co. Ltd. The content of poly(isobutylene) succinic anhydride in MOBILAD C2 07 is 0.76 mmol/g.
Blandingen ble omrørt ved 140°C i 2 timer ved hvilken tid infrarød spektroskopi indikerte over 95% omdannelse til suksinimidforbindelsen. The mixture was stirred at 140°C for 2 hours at which time infrared spectroscopy indicated over 95% conversion to the succinimide compound.
Emulqatorfremstillinq 2 (EP2)Emulsifier production 2 (EP2)
Fremgangsmåten fra EP1 ble gjentatt bortsett fra at blandingen ble omrørt ved 150°C i en time for å oppnå omtrent fullstendig omdannelse til imidkondensasjonsproduktet. The procedure from EP1 was repeated except that the mixture was stirred at 150°C for one hour to achieve almost complete conversion to the imide condensation product.
Emulqatorfremstillinq 3 (EP3)Emulsifier production 3 (EP3)
Fremgangsmåten fra EP1 ble gjentatt bortsett fra at Blandingen ble oppvarmet ved 120°C i 4-6 timer under vakuum. Det resulterende produktet omfattet over 80 vekt% av amidkon-densasj onsproduktet. The procedure from EP1 was repeated except that the mixture was heated at 120°C for 4-6 hours under vacuum. The resulting product comprised over 80% by weight of the amide condensation product.
Emulqatorfremstillinq 4 (EP4)Emulsifier production 4 (EP4)
Monoetanolamin og "MOBILAD"* C207 ble blandet i et målforhold på 1:1 med hensyn på poly(isobutylen)ravsyreanhydrid og blandingen ble tilbakeløpsbehandlet med toluen i et Dean og Stark-apparat i 3 timer ved 115"C etter hvilket tidspunkt vannfjerningen var fullstendig. Toluen ble så fjernet på en rotasjonsfordamper for å gi et kondensasjonsprodukt omfattende over 90 vekt% av suksiniminprodukt. Monoethanolamine and "MOBILAD"* C207 were mixed in a ratio of 1:1 with respect to poly(isobutylene)succinic anhydride and the mixture was refluxed with toluene in a Dean and Stark apparatus for 3 hours at 115°C after which time the water removal was complete The toluene was then removed on a rotary evaporator to give a condensation product comprising over 90% by weight of succinimine product.
Emulqatorfremstillinq 5 (EP5)Emulsifier production 5 (EP5)
Monoetanolamin og "MOBILAD"* C207 ble blandet i et målforhold på 1:1 med hensyn på poly(isobutylen)ravsyreanhydrid og blandingen ble tilbakeløpsbehandlet med toluen i et Dean og Stark-apparat i 3 timer ved 115°C etter hvilket tidspunkt vannfjerningen var fullstendig. Toluen ble så fjernet på en rotasjonsfordamper. Monoethanolamine and "MOBILAD"* C207 were mixed in a ratio of 1:1 with respect to poly(isobutylene)succinic anhydride and the mixture was refluxed with toluene in a Dean and Stark apparatus for 3 hours at 115°C after which time the water removal was complete . The toluene was then removed on a rotary evaporator.
Sammenlignende emulqatorfremstillinq A (CEPA)Comparative Emulsifier Preparation A (CEPA)
Monoetanolamin og MOBLIAD C207 ble blandet i et målforhold på 1:1 med hensyn til poly(isobutylen)ravsyreanhydrid og oppvarmet ved 60 til 80"C i 40 minutter. FTIR bekreftet et lavt nivå av suksinimidprodukt (typisk mellom 20 og 30%) og fravær av uomsatt anhydrid. Monoethanolamine and MOBLIAD C207 were mixed in a target ratio of 1:1 with respect to poly(isobutylene)succinic anhydride and heated at 60 to 80°C for 40 minutes. FTIR confirmed a low level of succinimide product (typically between 20 and 30%) and absence of unreacted anhydride.
Sammenlignende emulqatorfremstilling B (CEPB) Comparative Emulsifier Preparation B (CEPB)
Dimetylaminopropylamin og MOBILAD C2 07 ble blandet i et målforhold på 1:1 med hensyn til poly(isobutylen)ravsyreanhydrid og tillatt å reagere inntil i det vesentlige intet uomsatt anhydrid var igjen. Dimethylaminopropylamine and MOBILAD C2 07 were mixed in a target ratio of 1:1 with respect to poly(isobutylene)succinic anhydride and allowed to react until substantially no unreacted anhydride remained.
Eksempel 1 (El)Example 1 (Electricity)
Et emulsjonssprengstoff ble fremstilt ved hjelp av følgende fremgangsmåte. An emulsion explosive was prepared using the following procedure.
Ammoniumnitratet og kalsiumnitratet ble oppløst i vann ved en temperatur på 60'C og løsningen ble tilsatt til en omrørt blanding av destillat og emulgator. Omrøring ble fortsatt i en fast tidsperiode (105 sekunder) med en fast skjærhastighet (omrører gikk med 100 omdr.pr. min.) etter at det var dannet en emulsjon med jevn konsistens. The ammonium nitrate and calcium nitrate were dissolved in water at a temperature of 60°C and the solution was added to a stirred mixture of distillate and emulsifier. Agitation was continued for a fixed period of time (105 seconds) at a fixed shear rate (agitator running at 100 rpm) after an emulsion of uniform consistency had formed.
Eksempel 2 (E2)Example 2 (E2)
Fremgangsmåten fra El ble fulgt bortsett fra at pH i ammoniumnitrat/kalsiumnitrat-løsningen ble justert til 2,8. The procedure of E1 was followed except that the pH of the ammonium nitrate/calcium nitrate solution was adjusted to 2.8.
En emulsjon med viskositet på 2300 cP ble dannet. Etter 6 dagers lagring ved omgivelsestemperatur var emulsjonen i god tilstand. An emulsion with a viscosity of 2300 cP was formed. After 6 days of storage at ambient temperature, the emulsion was in good condition.
Sammenliqninqseksempel A CEAComparison example A CEA
Fremgangsmåten fra E2 ble fulgt bortsett fra at emulgatoren ble fremstilt ifølge CEPA. The procedure from E2 was followed except that the emulsifier was prepared according to CEPA.
Det ble dannet en emulsjon med en viskositet på 1600 cP. Oljefasen fra emulsjonen begynte å separere og ble observert som et separat sjikt over emulsjonen etter henstand over natten. An emulsion with a viscosity of 1600 cP was formed. The oil phase from the emulsion began to separate and was observed as a separate layer above the emulsion after standing overnight.
Eksempel 3 (E3)Example 3 (E3)
Et emulsjonssprengstoff ble fremstilt ved hjelp av følgende fremgangsmåte. An emulsion explosive was prepared using the following procedure.
Ammoniumnitratet og kalsiumnitratet ble oppløst i vann ved en temperatur på 60°C og løsningens pH ble justert til 3,8 med acetatbuffer. Løsningen ble tilsatt til en omrørt blanding av destilat og emulgator. Omrøring ble fortsatt i 60 sekunder ved 4 00 omdr. pr. min. for å danne en grov emulsjon. Den grove emulsjonen ble ytterligere raffinert i 90 sekunder ved 1500 omdr. pr. min. The ammonium nitrate and calcium nitrate were dissolved in water at a temperature of 60°C and the pH of the solution was adjusted to 3.8 with acetate buffer. The solution was added to a stirred mixture of distillate and emulsifier. Stirring was continued for 60 seconds at 400 rpm. my. to form a rough emulsion. The crude emulsion was further refined for 90 seconds at 1500 rpm. my.
Den grove emulsjonens viskositet var 640 cp. Den raffinerte emulsjonens viskositet var 450 cp. The viscosity of the crude emulsion was 640 cp. The viscosity of the refined emulsion was 450 cp.
Eksempel 4 (E4)Example 4 (E4)
Et emulsjonssprengstoff ble fremstilt ifølge E3 bortsett fra at emulgatoren ble fremstilt ifølge EP3. An emulsion explosive was prepared according to E3 except that the emulsifier was prepared according to EP3.
Den grove emulsjonens viskositet var 680 cp. Den raffinerte emulsjonens viskositet var 4100 cp. The viscosity of the crude emulsion was 680 cp. The viscosity of the refined emulsion was 4100 cp.
Sammenli<g>ningseksempel B (CEB)Comparative example B (CEB)
Et emulsjonssprengstoff ble fremstilt ifølge 3 bortsett fra at emulgatoren ble fremstilt ifølge CEPA. An emulsion explosive was prepared according to 3 except that the emulsifier was prepared according to CEPA.
Den grove emulsjonens viskositet var 560 cp. Den raffinerte emulsjonens viskositet var 3800 cp. The viscosity of the crude emulsion was 560 cp. The viscosity of the refined emulsion was 3800 cp.
Eksempel 5 (E4)Example 5 (E4)
Et emulsjonssprengstoff ble fremstilt ved hjelp av følgende fremgangsmåte. An emulsion explosive was prepared using the following procedure.
Ammoniumnitratet og kalsiumnitratet ble oppløst i vann ved en temperatur på 60°C og løsningens pH ble justert til 2,1. Løsningen ble tilsatt til en omrørt blanding av destillat og emulgator. The ammonium nitrate and the calcium nitrate were dissolved in water at a temperature of 60°C and the pH of the solution was adjusted to 2.1. The solution was added to a stirred mixture of distillate and emulsifier.
Omrøring ble fortsatt i 60 sekunder ved 400 omdr.pr. min. for å danne en grov emulsjon. Den grove emulsjonen ble ytterligere raffinert i 90 sekunder ved 1500 omdr. pr. minutt. Stirring was continued for 60 seconds at 400 rpm. my. to form a rough emulsion. The crude emulsion was further refined for 90 seconds at 1500 rpm. minute.
Ingen faseseparasjon ble observert etter 2 ukers lagring. No phase separation was observed after 2 weeks of storage.
Eksempel 6 (E6)Example 6 (E6)
Et emulsjonssprengstoff ble fremstilt ifølge E5 bortsett fra at emulgatoren ble fremstilt ifølge EP3. An emulsion explosive was prepared according to E5 except that the emulsifier was prepared according to EP3.
Ingen faseseparasjon ble observert etter 2 ukers lagring. No phase separation was observed after 2 weeks of storage.
Sammenliqninqseksempel C (CEC)Comparative Example C (CEC)
Et emulsjonssprengstoff ble fremstilt ifølge E5 bortsett fra at emulgatoren ble fremstilt ifølge CEPA. An emulsion explosive was prepared according to E5 except that the emulsifier was prepared according to CEPA.
Faseseparasjon, med et oljesj ikt på toppen av emulsjonen, ble observert innen en uke. Phase separation, with an oil layer on top of the emulsion, was observed within a week.
Eksempel 7 (E7)Example 7 (E7)
Et emulsjonssprengstoff ble fremstilt ved hjelp av følgende fremgangsmåte. An emulsion explosive was prepared using the following procedure.
Ammonium- og kalsiumnitratet ble oppløst i vann ved en temperatur på 60"C og løsningens pH ble justert til 2,2. Løsningen ble tilsatt til en omrørt blanding av destillat og emulgator. The ammonium and calcium nitrate were dissolved in water at a temperature of 60°C and the pH of the solution was adjusted to 2.2. The solution was added to a stirred mixture of distillate and emulsifier.
Omrøring ble fortsatt i 60 sekunder ved 4 00 omdr. pr. min. for å danne en grov emulsjon. Den grove emulsjonen ble ytterligere raffinert i 90 sekunder ved 1500 omdr. pr. min. Stirring was continued for 60 seconds at 400 rpm. my. to form a rough emulsion. The crude emulsion was further refined for 90 seconds at 1500 rpm. my.
Den raffinerte emulsjonens viskositet var 3.300 cp. Ingen faseseparasjon inntrådte etter 19 måneders lagring ved omgivelsestemperatur . The viscosity of the refined emulsion was 3,300 cp. No phase separation occurred after 19 months of storage at ambient temperature.
Sammenli<q>nin<q>seksempel D (CED)Compar<q>nin<q>six example D (CED)
Et emulsjonssprengstoff ble fremstilt ifølge E7 bortsett fra at emulgatoren var fremstilt ifølge (CEPB). An emulsion explosive was prepared according to E7 except that the emulsifier was prepared according to (CEPB).
Den raffinerte emulsjonens viskositet var 1200 cp. Et oljesj ikt på toppen av emulsjonen oppsto innen 12 dager. The viscosity of the refined emulsion was 1200 cp. An oil layer on top of the emulsion appeared within 12 days.
Eksempel 8 (E8)Example 8 (E8)
Et emulsjonssprengstoff av den type som er egnet for bruk som et pakket sprengstoff ble fremstilt ved bruk av følgende bestanddeler. Den brukte emulgatoren var emulgator nr. 1. An emulsion explosive of the type suitable for use as a packaged explosive was prepared using the following ingredients. The emulsifier used was emulsifier No. 1.
Emulgatoren ble tilsatt til oljefasen ved en temperatur på 90°C, idet oljefasen besto av voksen og parafinoljebestanddelene. The emulsifier was added to the oil phase at a temperature of 90°C, the oil phase consisting of the wax and the paraffin oil components.
En grov emulsjon ble fremstilt ved tilsetning av den vandige fasen, bestående av en løsning av nitratsaltbestanddelene i vann, til oljefasen ved omtrent 90"C. Blandemaskinen ble operert med en visp på en hastighet 2 i to minutter fulgt av ytterligere ti minutter ved hastighet 3 for å oppnå den primære emulsjonen. A coarse emulsion was prepared by adding the aqueous phase, consisting of a solution of the nitrate salt constituents in water, to the oil phase at about 90°C. The mixer was operated with a whisk at speed 2 for two minutes followed by a further ten minutes at speed 3 to obtain the primary emulsion.
Den primære emulsjonens viskositet var 316.000 cp vedThe primary emulsion viscosity was 316,000 cp at
11°C. Emulsjonens dråpestørrelse er typisk i området 2 til 411°C. The emulsion's droplet size is typically in the range 2 to 4
pm. Emulsjonens ledningsevne ved 75°C var 300 + 100 pSm-<1>.p.m. The conductivity of the emulsion at 75°C was 300 + 100 pSm-<1>.
En del av den primære emulsjonen ble lagret ved omgivelsestemperatur. Krystallinnholdet i den primære emulsjonen var meget lavt etter 27 måneder. A portion of the primary emulsion was stored at ambient temperature. The crystal content of the primary emulsion was very low after 27 months.
Til en andre porsjon ble aluminium og mikroballonger forsiktig tilblandet. Blandingen ble så blandet med en bladrører i 2,5 minutter ved hastighet 1. Krystallinnholdet i den avkjølte emulsjonen var også lavt. For a second portion, aluminum and microballoons were carefully mixed. The mixture was then mixed with a blade stirrer for 2.5 minutes at speed 1. The crystal content of the cooled emulsion was also low.
Sammenliqninqseksempel E (CEE)Comparative example E (CEE)
Et emulsjonssprengstoff av den type som er egnet for bruk som et pakket sprengstoff ble fremstilt ifølge E8 bortsett fra at emulgatoren var fremstilt ifølge CEPA. An emulsion explosive of the type suitable for use as a packaged explosive was prepared according to E8 except that the emulsifier was prepared according to CEPA.
Den primære emulsjonens viskositet var 2 60.000 cp vedThe viscosity of the primary emulsion was 260,000 cp at
77 °C. Emulsjonens dråpestørrelse var typisk i området 3 til77 °C. The emulsion droplet size was typically in the range of 3 to
6 pm. Emulsjonens ledningsevne ved 75°C var 300 + 100 pSm-<1>. 6 p.m. The conductivity of the emulsion at 75°C was 300 + 100 pSm-<1>.
Krystallinnholdet i den primære emulsjonen var meget lavt etter 2 8 måneders lagring ved omgivelsestemperatur. The crystal content of the primary emulsion was very low after 28 months of storage at ambient temperature.
Eksempel 9 (E9)Example 9 (E9)
Et emulsjonssprengstoff av en type som er egnet for bruk som et pakket sprengstoff ble fremstilt ifølge E8 bortsett fra at emulgatoren var fremstilt ifølge EP5. An emulsion explosive of a type suitable for use as a packaged explosive was prepared according to E8 except that the emulsifier was prepared according to EP5.
Den primære emulsjonen hadde en viskositet på 3 00.000 cp ved 77 °C. Emulsjonens dråpestørrelse var typisk i området 1 til 3 pm. The primary emulsion had a viscosity of 300,000 cp at 77°C. The emulsion droplet size was typically in the range of 1 to 3 µm.
Sammenliqninqseksempel F (CEF)Comparison example F (CEF)
Et emulsjonssprengstoff av den type som er egnet for bruk som et pakket sprengstoff, ble fremstilt ifølge E9 bortsett fra at emulgatoren var fremstilt ifølge CEPB. An emulsion explosive of the type suitable for use as a packaged explosive was prepared according to E9 except that the emulsifier was prepared according to CEPB.
Den primære emulsjonens viskositet var 280.000 cp ved 77°C. Emulsjonens dråpestørrelse var typisk i området 2 til 4 pm. The primary emulsion viscosity was 280,000 cp at 77°C. The emulsion droplet size was typically in the range of 2 to 4 µm.
Eksempel 10 (E10)Example 10 (E10)
En emulsjon av den type som er egnet for bruk som et massesprengstoff ble fremstilt ved bruk av følgende bestanddeler i hvilke emulgatoren ble fremstilt. An emulsion of the type suitable for use as a mass explosive was prepared using the following ingredients in which the emulsifier was prepared.
En vandig løsning ble fremstilt ved å blande ammoniumnitratet og vann ved70°C og denne løsning ble tilsatt ved rask omrøring til en blanding av emulgatoren og destillat ved 80°C. An aqueous solution was prepared by mixing the ammonium nitrate and water at 70°C and this solution was added with rapid stirring to a mixture of the emulsifier and distillate at 80°C.
Den tid som var krevet for å oppnå en emulsjonsviskositet på 24 Pa.s. ved bruk av en fast fremgangsmåte, ble styrt. Dette taes som en indikator på lett raffinering. The time required to achieve an emulsion viscosity of 24 Pa.s. using a fixed method, was controlled. This is taken as an indicator of light refining.
Raffineringstiden ble observert å være 9,5 minutter. Emulsjonens ledningsevne ble funnet å være 2 00 pSm-<1>ved 20°C. Krystallinnholdet i emulsjonen etter 3 måneder var ganske lavt. The refining time was observed to be 9.5 minutes. The conductivity of the emulsion was found to be 200 pSm-<1> at 20°C. The crystal content in the emulsion after 3 months was quite low.
Sammenliqninqseksempel G (CEG)Comparison example G (CEG)
Et emulsjonssprengstoff av den type som er egnet som et massesprengstoff ble fremstilt ifølge E10 bortsett fra at emulgatoren var fremstilt ifølge CEPA. An emulsion explosive of the type suitable as a bulk explosive was prepared according to E10 except that the emulsifier was prepared according to CEPA.
Raffineringstiden ble observert å være 11 minutter. Emulsjonens ledningsevne ble funnet å være pSm--*- ved 2 0°C. Krystallinnholdet i emulsjonen etter 3 måneder var lavt. The refining time was observed to be 11 minutes. The conductivity of the emulsion was found to be pSm--*- at 20°C. The crystal content in the emulsion after 3 months was low.
Sammenliqninqseksempel H (CEH)Comparative example H (CEH)
Et emulsjonssprengstoff av den type som er egnet for anvendelse som et massesprengstoff ble fremstilt ved bruk av følgende bestanddeler. An emulsion explosive of the type suitable for use as a mass explosive was prepared using the following ingredients.
En vandig løsning ble fremstilt ved å blande ammoniumnitratet og vann ved 70°C og denne løsning ble tilsatt ved rask omrøring til en blanding av sorbitan, monooleat og destillat ved 80°C. An aqueous solution was prepared by mixing the ammonium nitrate and water at 70°C and this solution was added with rapid stirring to a mixture of sorbitan, monooleate and distillate at 80°C.
Raffineringstiden ble observert å være 9 minutter. Dråpestørrelsen ble observert å være i området 3 til 10 pm. Emulsjonens ledningsevne var 13900 pSm-<1>. The refining time was observed to be 9 minutes. The droplet size was observed to be in the range of 3 to 10 pm. The conductivity of the emulsion was 13900 pSm-<1>.
Emulsjonen ble lagret ved omgivelsestemperatur i 4 måneder og krystallisasjonsnivået ble observert å være meget utstrakt. The emulsion was stored at ambient temperature for 4 months and the level of crystallization was observed to be very extensive.
Claims (10)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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AUPI691988 | 1988-02-23 |
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NO890754D0 NO890754D0 (en) | 1989-02-22 |
NO890754L true NO890754L (en) | 1989-08-24 |
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NO89890754A NO890754L (en) | 1988-02-23 | 1989-02-22 | EXPLANATORY MIXTURE, AND PROCEDURE FOR PREPARING SUCH A. |
Country Status (15)
Country | Link |
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US (1) | US4999062A (en) |
EP (1) | EP0330375A1 (en) |
JP (1) | JP3169947B2 (en) |
CN (1) | CN1111226A (en) |
CA (1) | CA1329324C (en) |
GB (1) | GB2216129A (en) |
MW (1) | MW889A1 (en) |
MX (1) | MX169281B (en) |
MY (1) | MY103827A (en) |
NO (1) | NO890754L (en) |
NZ (1) | NZ227918A (en) |
PH (1) | PH26513A (en) |
ZA (1) | ZA891112B (en) |
ZM (1) | ZM1189A1 (en) |
ZW (1) | ZW2689A1 (en) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
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US4828633A (en) | 1987-12-23 | 1989-05-09 | The Lubrizol Corporation | Salt compositions for explosives |
US4931110A (en) * | 1989-03-03 | 1990-06-05 | Ireco Incorporated | Emulsion explosives containing a polymeric emulsifier |
US5160387A (en) * | 1989-11-16 | 1992-11-03 | Ici Australia Operations Proprietary Limited | Emulsion explosive |
CA2049628C (en) * | 1991-08-21 | 2002-02-26 | Clare T. Aitken | Vegetable oil emulsion explosive |
US5920031A (en) * | 1992-03-17 | 1999-07-06 | The Lubrizol Corporation | Water-in-oil emulsions |
GB9511701D0 (en) * | 1995-06-09 | 1995-08-02 | Burwood Corp The Ltd | Composition |
DE19847868C2 (en) | 1998-10-16 | 2003-09-25 | Clariant Gmbh | Explosives containing modified copolymers of polyisobutylene and maleic anhydride as emulsifiers |
EP1254090A2 (en) | 2000-01-25 | 2002-11-06 | The Lubrizol Corporation | Water in oil explosive emulsions |
DE10003297C2 (en) | 2000-01-27 | 2003-08-21 | Clariant Gmbh | Explosives containing modified copolymers of polyisobutylene, vinyl esters and maleic anhydride as emulsifiers |
US20030130135A1 (en) * | 2001-11-13 | 2003-07-10 | Crompton Corporation | Emulsifier for oil-based drilling fluids |
AU2010248022C1 (en) | 2009-05-15 | 2020-01-16 | The Lubrizol Corporation | Quaternary ammonium amide and/or ester salts |
CN104003826B (en) * | 2014-04-30 | 2016-04-27 | 安徽江南化工股份有限公司 | A kind of preparation method using liquid ammonium nitrate production powdery emulsifying explosive |
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Publication number | Priority date | Publication date | Assignee | Title |
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US3269946A (en) * | 1961-08-30 | 1966-08-30 | Lubrizol Corp | Stable water-in-oil emulsions |
US3378494A (en) * | 1964-08-07 | 1968-04-16 | Shell Oil Co | Water-in-oil emulsion fluids |
CA1146944A (en) * | 1979-12-20 | 1983-05-24 | Peter J.N. Brown | Lubricant additives, their method of preparation and lubricants containing them |
GB2156799B (en) * | 1984-03-21 | 1987-12-16 | Ici Plc | Emulsion explosive |
ZW23786A1 (en) * | 1985-12-06 | 1987-04-29 | Lubrizol Corp | Water-in-oil-emulsions |
US4844756A (en) * | 1985-12-06 | 1989-07-04 | The Lubrizol Corporation | Water-in-oil emulsions |
US4708753A (en) * | 1985-12-06 | 1987-11-24 | The Lubrizol Corporation | Water-in-oil emulsions |
MW787A1 (en) * | 1986-02-28 | 1987-10-14 | Ici Australia Ltd | Explosive composition |
US4828633A (en) * | 1987-12-23 | 1989-05-09 | The Lubrizol Corporation | Salt compositions for explosives |
US4919178A (en) * | 1986-11-14 | 1990-04-24 | The Lubrizol Corporation | Explosive emulsion |
US4840687A (en) * | 1986-11-14 | 1989-06-20 | The Lubrizol Corporation | Explosive compositions |
US4863534A (en) * | 1987-12-23 | 1989-09-05 | The Lubrizol Corporation | Explosive compositions using a combination of emulsifying salts |
MW1888A1 (en) * | 1987-06-29 | 1989-03-08 | Aeci Ltd | Explosive |
GB8822187D0 (en) * | 1988-09-21 | 1988-10-26 | Ici Plc | Water-in-oil emulsion explosive |
-
1989
- 1989-02-09 NZ NZ227918A patent/NZ227918A/en unknown
- 1989-02-13 ZA ZA891112A patent/ZA891112B/en unknown
- 1989-02-16 GB GB8903487A patent/GB2216129A/en not_active Withdrawn
- 1989-02-16 EP EP89301503A patent/EP0330375A1/en not_active Withdrawn
- 1989-02-20 MW MW8/89A patent/MW889A1/en unknown
- 1989-02-20 ZM ZM11/89A patent/ZM1189A1/en unknown
- 1989-02-20 MY MYPI89000206A patent/MY103827A/en unknown
- 1989-02-22 NO NO89890754A patent/NO890754L/en unknown
- 1989-02-22 JP JP04040889A patent/JP3169947B2/en not_active Expired - Lifetime
- 1989-02-23 CA CA000591916A patent/CA1329324C/en not_active Expired - Lifetime
- 1989-02-23 US US07/313,846 patent/US4999062A/en not_active Expired - Lifetime
- 1989-02-23 ZW ZW26/89A patent/ZW2689A1/en unknown
- 1989-02-23 MX MX015046A patent/MX169281B/en unknown
- 1989-04-21 PH PH38223A patent/PH26513A/en unknown
-
1995
- 1995-03-31 CN CN95103980A patent/CN1111226A/en active Pending
Also Published As
Publication number | Publication date |
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ZM1189A1 (en) | 1989-10-27 |
PH26513A (en) | 1992-08-07 |
MY103827A (en) | 1993-09-30 |
US4999062A (en) | 1991-03-12 |
GB2216129A (en) | 1989-10-04 |
MX169281B (en) | 1993-06-28 |
NO890754D0 (en) | 1989-02-22 |
JPH01261290A (en) | 1989-10-18 |
CA1329324C (en) | 1994-05-10 |
ZA891112B (en) | 1989-10-25 |
MW889A1 (en) | 1989-10-11 |
CN1111226A (en) | 1995-11-08 |
EP0330375A1 (en) | 1989-08-30 |
NZ227918A (en) | 1992-03-26 |
GB8903487D0 (en) | 1989-04-05 |
ZW2689A1 (en) | 1989-11-01 |
JP3169947B2 (en) | 2001-05-28 |
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